Dimethylamine → 3-(1-{[2-(dimethylamino)ethyl]sulfonyl}-4-piperidinyl)-5-phenyl-1H-indole-7-carboxamide

HRID 2267510Notes

Reaction equation

Cl[CH2:2][CH2:3][S:4]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[C:21]3[C:16](=[C:17]([C:28]([NH2:30])=[O:29])[CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:8]1)(=[O:6])=[O:5].[CH3:31][NH:32][CH3:33].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC#N>[CH3:31][N:32]([CH3:33])[CH2:2][CH2:3][S:4]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[C:21]3[C:16](=[C:17]([C:28]([NH2:30])=[O:29])[CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:8]1)(=[O:6])=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide (26 mg, 0.063 mmol) in CH3CN (5 mL), dimethylamine (0.16 mL, 0.315 mmol), K2CO3 (35 mg, 0.252 mmol) and NaI (cat. 0.5 mg) were added. The reaction mixture was stirred at 80° C. for 16 hours. The solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate, filtered and the solvent removed under reduced pressure. The resulting residue was purified by reverse phase HPLC (CH3CN/water, 0.1% TFA) to give title compound (14 mg, 48%).

Workup

customThe solvent was removed under reduced pressure
customThe residue was partitioned between ethyl acetate and water
dry with materialThe organic phase was dried over magnesium sulfate
filtrationfiltered
customthe solvent removed under reduced pressure
customThe resulting residue was purified by reverse phase HPLC (CH3CN/water, 0.1% TFA)

Sources & evidence

ORD record: ord-75ff698322674d04811461320869195c
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858796B2

Reaction notes

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